I feel the same way at OP, amazing guests, but can't he push them a bit?
What I'd like is more like what Tyler Cowen does, on non-tech subjects [1]. He gives the impression of having read all their books (and their opponents') not just having skimmed Wikipedia over breakfast. He keeps it moving, and often gets people a little bit off-balance, not aggressively, but enough to make people think afresh and not just repeat what they always say.
Besides people's work, he'll ask them serious questions about (say) their known interest in some kinds or Jazz, or unrelated things about characters they would have run into at MIT in the 70s, or about the Russian education system. (I presume he has people helping him prepare, but maybe he's just like this all the time.)